Dear Dude: How To Rock A First Date

This is one of our semi-regular Dear Dude columns in which my real-life friend The Dude answers your questions about the hairier sex. Dear Dude is an industrial designer with a weakness for bikes, dogs, good food and smart ladies.

Dear Dude,
What are the best/worst things that a guy/girl can do on a first date?

Can’t get a 2nd Date

Ok – you asked for it!

Instead of drawing up two columns with the headings “best” and “worst”, I’ll just spout some nonsense about dating, all of which is my opinion alone, and not supported by anything other than my own personal experience. I imagine these things go for both men and women.

I don’t care if you think I am shallow for saying this, but look like your picture.
I can’t this stress enough – If you are online dating, please please please; as much for your sake as mine, please use current, un-retouched pictures. I cannot tell you how disappointing it is to meet the “cute” girl I chatted with twice online, in person; and she is clearly not as young, cute, fit, or clever as I was led to believe.

The fairytale ending does not exist when you lie. You will not get me to fall in love with your messages, your voice or the picture of you from high school where people told you you look “old for your age.” Embrace who you are and what you look like. Everyone is “trying to lose a few pounds.” Saying you “gained some weight this winter” is not an excuse to use photos from five years ago. This goes for guys too – yes, she will notice when you don’t look like your picture!

It is good and polite to show up on time or within 5-10 minutes
But don’t get too upset with him (or her) for being a bit late (just store it away in the date-a-base – “showed up late, -5 points.”) If you are perpetually late – say so. Be honest and avoid dumb excuses. “I left my house late and I didn’t account for traffic” is perfectly acceptable once or twice.

Don’t wear excessive makeup (or any at all, in my opinion)
I would rather be presented with a “less attractive,” unmade-up real “you” than the best mask Lancome or CoverGirl can create. I feel like using make-up is like a little lie. The more used, the bigger the lie. That said, If I can’t tell, I don’t know 😉

Avoid dinner and/or movie on the first date
A quick “get to know you” coffee or drink could save you both a lot of time and uncomfortable silence.

Drink something classy yet unpretentious and don’t get blotto
This should not need explanation.

Suggest going dutch if you get snacks or the drink bill isn’t split up
Unless he slurped down 5 beers for each of your one, don’t get hung up on money. If it was a good date, it should even out over several dates. If it wasn’t, consider it a “poor judgment tax.” I think the worst thing a date can do is assume you are covering the bill and never even offer.

*sidenote from Sarah: I will totally offer to split the bill on the first date, but if the guy makes significantly more money than I do, I think a gentleman would insist of paying the whole thing. Just my two cents.

Most importantly: relax, be yourself and don’t talk just to fill space

Acting too eager and excited can actually be a turn off to some. And acting ‘too cool for school’ can be a turn off, too. This first date is not everything – there are other guys (or girls) out there for you, aside from this person you hardly know.

Ask questions and pay attention. Smile and have fun! Try not to go into the date with notions about the person based on what (little) you know about them but remain pragmatic and watch for signs of incompatibly. Don’t be afraid of rejection, rejecting or admitting incompatibility; be honest (and sensitive) about it. Give your date a chance to be themselves by avoiding absolutes (“I never date men/women shorter than 5’10” – for example).

So there you go, the Dude’s Loose Guidelines To Dating.

As always, I welcome any additional “rules” or guidelines the readers have in the comments!


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  1. LC

    Thank you, Dude! I just had a first date last night and this morning was like "Oh, man, I went dutch on this date, didn't I read somewhere that the guy is always supposed to pay on the first date?" and got all insecure about it. But you have calmed my fears.

    Also, it's like you read my mind with this post today. Thanks!

  2. iris

    Yeah, the pay-on-the-first-date thing is totally a toss up. As a female, I'll offer once, but never insist on paying/splitting. If the dude really wants to pay, let 'im pay.

    …otherwise, I just pay for the next date.

  3. JoAnna

    The gentleman thing goes both ways – a true lady would be just as insistent about paying the entire bill if she knows she makes a lot more than her date.

  4. Kelsi

    Good advice, Dude. I tend not to over-analyze the bill-paying scenario, but I did have one experience that raised my eyebrows a little: I was out for a drink with a guy, and things were going well. Then he invited me to go back to his place. When it came time to pay the bill, he told me he was between jobs and couldn't pay for anything more than the (three) beers he had.

    At first I felt bad because I wasn't aware of his financial situation and didn't want to be insensitive. But then I wondered, "Why didn't we go somewhere for a free date, like to the park or the lake or go for a walk?" The red flags started to appear, so I paid my tab and I backed out.

    When I dismissed his invitation for a second date he got very mad and said I must only be after people with money. No, I'm looking for people who manage their money WISELY. I have no problem paying my own way, and I understand the job market is terrible right now, so what would have impressed me is a creative, cost-free date alternative.

  5. Laura

    Hmmmm, I'm actually not sure I agree with all of this. I don't think it's reasonable to ask a girl not to wear any makeup. I don't think it's a lie unless you're donning a full-on kabuki theatre face (and I'm not sure that would make you look your best anyway). Everyday makeup just adds polish. I think women look a little strange if they're all dressed up in a fancy dress, nice shoes, painted nails, and then bare face… it's like you ran out of time to finish getting ready. Besides, is it also lying if we wear a shirt that plays up our awesome shoulders and downplays a little belly? I don't think so.

    As for who pays, I think it should be whomever did the asking out. If a guy asks me out, I will offer to pay (and I will pay if he takes me up on it), but I think it's rude if he takes me up on the offer. I'll pay on the second date.

  6. Anne

    No make-up eh?

    What are your thoughts on push-up bras? 😉

    I've always wondered about this since I saw that Will and Grace episode with the water bra.

  7. Jennifer

    I read somewhere that the dating etiquette is that the person who asked for the date is the one who should pay the bill.
    Although i am used to spliting the bill, I recently went on a date where the guy insisted on paying which made a rather nice change 🙂

  8. Sarah Von Bargen


    I totally agree! Also, I won't let a guy pay for me if I'm not interested in seeing him again.

    I mean, I don't get all "Um, no. We're splitting it because I hatechu." but I'm much more likely to politely try to pay for my nachos and beer 😉

  9. fawn

    Be yourself, but don't do this, this, and this.

  10. Lila

    Yeah, not on board with the "no makeup" comments. Makeup isn't a "lie," it's a means of self-expression, just like clothes and hairstyles. I'm not trying to fool unsuspecting men into thinking I'm a beauty queen (it wouldn't work even if I was!), I'm enhancing my best features and being creative, just like when I put together a flattering outfit.

    Guys who assume that women who wear a lot of makeup are shallow or devious or whatever are really only proving that THEY judge people based on appearances, IMHO.

  11. lucia

    I'm a complete beginner: how do you end the first date when you're not interested? Do you say, oh, well, never mind? Or pretend you'll call? What's the best way to do that?

  12. Anonymous

    no offense, but this list reminds me of why I avoid dating like the plague and prefer to focus on friendships first and leave room for them to develop into more. it's easier to figure out if you and someone else will "work out" when you actually know and understand each other.
    as another commenter said, on dates it's like "be yourself but don't do this, don't say this, don't be too eager, don't be too uninterested." With so much pressure to appear "cool but not too cool" , how can two people really let loose and be honest? First dates are more stressful to me than job interviews as a result.

    If wearing makeup is lying, is shaving your legs also being false?

  13. Anonymous

    as a person who won`t have premarital sex, I wonder how early on in the dating scenario I should let the guy know this? It seems too personal for the first date, but I don't want to lead a guy on if he thinks that after a few dates, we'll be having sex…

  14. Rebecca

    The "no makeup" comment definitely rubbed me the wrong way.

    We all have ways that we like to express ourselves; wearing makeup, wearing certain clothes, shaving, styling our hair. It isn't wearing a mask or being false, it is a means of self-expression. You are free to be attracted to women who don't wear makeup, but don't put it out there as a rule for all dating women. Makeup isn't inherently and, and saying so goes against the "be yourself" advice and seems pretty judgmental.

    I also wouldn't waste a lot of energy ordering the perfect drink just to impress a date, but that is a whole different topic.

  15. The Naked Redhead

    @lucia–My rules for a date where you're not interested is to set the whole thing up for a "win" beforehand…like Dude mentioned, keep the first date short and simple. That way, if there is awkwardness, you're not stuck in a 2 hour dinner or movie.

    Second, if there's no connection, no big deal. I'm a big fan of things living or dying organically. That being said, if the other party seems significantly more interested than you are, I don't think it's wrong to say, "Thanks for meeting me out, but I'm getting more of a friend vibe, if that's cool." I've done this a couple of times on dates, and have always been met with a very positive reaction from the guy. It saves us both time, and me the awkwardness of ignoring his texts later. 🙂

  16. margosita

    I'd say the "no make-up" idea should be something like "Don't wear more make-up than you normally do." If you have a standard amount that is what you put on every morning, don't deviate or try to doll-up to more impressive standards.

    That pretty much aligns with the "be yourself" rule, I think.

  17. the_Mann!

    Clearly we're all forgetting that some people actually dont care how much make up you put on, whether you shaved too much or not, what they care about is that the person is presentable and they are comfortable in who they are, in any case this person never saw you before so they dont know how much make up you have been putting on! The whole point should be not how you act strange to impress but how you can be yourself and impress! So there's no point in this rules, such articles actually cause alot of 'nerves' during dates…so, if someone likes you, good, if they don't, too bad, dont pretend!

  18. Anonymous

    i know


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